Obturator Hernia (OH) is a rare type of pelvic hernia in which abdominal contents protrude through the obturator canal. This condition can lead to bowel obstruction, gangrene, or ischaemia, all of which pose significant risks and can be life-threatening. OH predominantly affects elderly, thin females and often remains asymptomatic until there is compression of the obturator nerve. As a result, OH should be considered in the differential diagnosis of intestinal blockages of unknown origin. For preoperative diagnosis, Computed Tomography (CT) is regarded as the optimal imaging modality. However, Ultrasonography (USG) may sometimes misidentify it as a femoral or inguinal hernia. Due to its non specific symptoms and clinical presentations, early preoperative identification of OH can be challenging. Hereby, the authors present a case of OH in an 80-year-old male patient with biopsy-proven prostate carcinoma who reported burning sensations and difficulty in micturition over the past month. His medical history included insulin-managed diabetes and extensive alcohol consumption. Physical examination revealed a non tender swelling on the medial aspect of the right upper thigh, prompting imaging studies that included a Kidney, Ureter, and Bladder (KUB) radiograph and a CT-KUB. The radiograph showed a radiolucent area in the right obturator canal, while the CT confirmed the diagnosis, revealing a herniated sac within the obturator externus muscle, measuring 61x109x89 mm, with associated bone remodelling of the pubic symphysis and mild prostatomegaly. Despite understanding the risks, the patient has not yet undergone surgery due to his age and co-morbidities. The present case underscores the need for heightened awareness of OH in elderly males, especially those with significant medical histories, as early recognition and intervention are crucial to preventing serious complications.